Regio- and Stereoselective Synthesis of b-D-Gluco-, a -L-Ido-and a -L-Altro pyranosiduronicAcids from D 4-Uronates

No Thumbnail Available
Authors
Bazin, H.G.
Wolff, M.W.
Linhardt, Robert J.
Issue Date
1999
Type
Article
Language
ENG
Keywords
Biology , Chemistry and chemical biology , Chemical and biological engineering , Biomedical engineering
Research Projects
Organizational Units
Journal Issue
Alternative Title
Abstract
The stereoselective synthesis of B-D-glucopyranosiduronic, R-L-idopyranosiduronic, and R-L-altro-pyranosiduronic acids has been performed from different ∆4-uronate monosaccharides. Bromination of the C-4,5 double bond provided the trans-diaxial bromohydrin derivatives, which were converted to the corresponding epoxides in high yields. Direct reduction of the epoxides using borane-tetrahydrofuran complex led to the corresponding glucuronic acids in low to good yields. Glucuronic acids were also obtained in satisfactory yields through a two-steps procedure involving bromination of the epoxide with titanium(IV) bromide followed by reduction using tributyltin hydride. Lewis acid-catalyzed rearrangement of these epoxides led to the corresponding R-L C-4 ketopyranosides adopting the 1C4 chair conformation. Hydride reduction afforded the R-L-idopyranosiduronic or the R-L-altropyranosiduronic acids, the stereoselectivity of the reduction being controlled by the appropriate substitution pattern.
Description
Journal of Organic Chemistry, 64, 144-152
Note : if this item contains full text it may be a preprint, author manuscript, or a Gold OA copy that permits redistribution with a license such as CC BY. The final version is available through the publisher’s platform.
Full Citation
Regio- and Stereoselective Synthesis of b-D-Gluco-, a -L-Ido-and a -L-Altro pyranosiduronicAcids from D 4-Uronates, H. G. Bazin,M.W. Wolff, R.J. Linhardt, Journal of Organic Chemistry, 64,144-152, 1999.
Publisher
Terms of Use
Journal
Volume
Issue
PubMed ID
DOI
ISSN
EISSN